"from Kansas City days and the mores of different parts of that city, Chicago and the lake boats."
Ernest Hemingway, circa 1917 Oak Park, Illinois
Public DomainErnest Hemingway, circa 1917 

Being all of twenty-three when he first met Stein, Hemingway would have spent the majority of the preceding years in the Chicago suburb where he was born and raised. Upon graduating from Oak Park and River Forest High School in 1917, Hemingway would be given three choices: either he could continue his education at college, he could join the war, or he could begin a career.

Dr. Hemingway, keen to keep his son away from the fighting, made arrangements for Ernest to start work at The Kansas City Star in October. Although his father's efforts were short-lived -- Hemingway would remain cub reporter for a period of just six months before going to the Italian front as an ambulance driver -- his experiences in Kansas City clearly left an impression, reappearing in various formats throughout his subsequent stories. 'Kansas City', he would comment, 'was a strange and wonderful place'. 

Between 1920 and 1921 -- just before the move to Paris -- Hemingway gained more of an understanding of Chicago. He worked as a reporter for the Toronto Star, and met and fell in love with Hadley.

Wedding of Hadley Richardson and Ernest Hemingway Horton's Bay, Michigan
Public DomainWedding of Hadley Richardson and Ernest Hemingway Horton's Bay, Michigan - Credit: Ernest Hemingway Photograph Collection, John F. Kennedy Presidential Library and Museum, Boston.